Dodecanedioic acid is commerically prepared by the air oxidation of cyclododecane thus forming cyclododecanol or cyclododecanone. These compounds are then oxidized to dodecanedioic acid by nitric acid. Such a process is disclosed in U.S. Pat. No. 3,637,832.
The oxidation of olefins to aldehydes, ketones and carboxylic acids by the use of ruthenium and cerium salt is disclosed in U.S. Pat. No. 3,459,644 to MacLean et al.
U.S. Pat. No. 5,026,461 to Davis et al. discloses preparation of dodecanedioic acid by the oxidation of cyclododecene by the use ruthenium and cerium salts in a two phase mixture.
The oxidation of saturated cyclohydrocarbons to dioic acids using ruthenium tetroxide with a two-phase system in which the oxidation takes place in the organic phase and the ruthenium dioxide formed in the organic phase is oxidized to ruthenium tetroxide by sodium hypochlorite in the aqueous phase is disclosed in J. Org. Chem., Vol. 40, No. 17, 1975 on pp. 2539-40 by Spitzer et al.
The oxidation of alcohols to carbonyl compounds using a two-phase system employing ruthenium tetroxide as the oxidizing agent in the organic phase, and in which the ruthenium dioxide formed is oxidized indirectly by electrolysis in the aqueous phase back to the tetroxide is disclosed in J. Org. Chem., Vol. 51, pp. 155-161, (1986).
The electrolytic oxidation of cerium +3 ions to cerium +4 ions, and the use of cerium +4 ions as the oxidizing agent in the oxidation of aromatic compounds to carbonyl containing compounds in methanesulfonic acid is disclosed in U.S. Pat. No. 4,639,298 to Kreh.